Though I can't help but wonder if, even though Bosco knew Faith was just having a quasi-breakdown, he was affected by her tongue-lashing. I think that's what prompted him to "lose the evidence" in the first place. I remember Bosco asking his superior how many people he arrested as he was doing all the paperwork for them, and his superior answered with "Almost the entire neighborhood."
That says something, don' it? 0_0

As for this hooker/chief dilema, I didn't remember hearing the hooker say such before, but with that now in my head, what you say makes sense.